


The Principal Will See You Now

by somewhereelse



Category: Arrow (TV 2012)
Genre: Alternate Universe, F/M, High School, Mild Language
Language: English
Status: Completed
Published: 2018-08-29
Updated: 2018-09-19
Packaged: 2019-07-04 07:51:44
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 19,496
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15836973
Author URL: https://archiveofourown.org/users/somewhereelse/pseuds/somewhereelse
Summary: When Robert and Moira leave for a second honeymoon in a bid to save their marriage, Oliver is left in charge of teenaged Thea. He quickly realizes that Thea’s taking after him in the worst of ways, and coincidentally every teacher at Starling City Prep agrees. So the prioritized to-do list goes: keep her alive; get her to sit through a full day of school; and convince her to dump the good-for-nothing boyfriend. Frustrating his attempt at playing responsible big brother is a complicated relationship with Thea’s new principal, one Felicity Smoak.





	1. Chapter 1

**Author's Note:**

> This really is not anywhere near as porn-esque as the title implies.

  
  
  


 

“What the hell, Ollie?”

Thea’s not at all subtle when she finds him leaning against the lamppost opposite the side exit to the basketball gym. Yes, there are multiple gyms dedicated to single sports, an Olympic-sized pool, and indoor tennis courts at the school. Most of which were built courtesy of donations from the Queen and Merlyn families approximately ten years ago.

“Go back to class,” he instructs in a bored tone. When he looks up from his phone, Thea’s still standing there, embarrassed and angry. “I’m serious. If you think I have something better to do than catch you every time you try to sneak out of this school, you’re wrong. Go back to class.”

Thea scoffs, crossing her arms over chest. “You can’t just hang out at a high school all day like some pedo. They’re going to call the cops on you.”

Smugly, Oliver grins at his little sister. “I already talked to the security officer. He’s completely fine with it. Especially since I know every way out of this place. Go back to class.”

“You’re the worst!” is her final parting shot before disappearing back inside.

He jogs around the building and cuts across the soccer fields to reach the east side of the recreation area. Not three minutes later, he hears someone entering the pool area. Thea peeks through the wrought iron fence and spies him waiting.

“Go back to class.”

“I hate you!”

“That’s fine but I can do this all day!” His victory is cut short by a very distinctive voice calling his name from behind. Ah,  _shit._

 

* * *

 

“Mr. Queen.”

Vice Principal Walter Steele can’t seem to stop calling him by his last name. After the man all but dragged him into his office and plopped his ass into a wooden chair that he was once intimately familiar and does not at all miss, Oliver thinks they should be past this formality. He hasn’t even been a student here in over a decade.

“Is this really necessary?” By Mr. Steele’s long-suffering sigh, the answer is  _yes_.

“The principal requested that I speak with you.”

Oliver lets out a low whistle. “The head honcho, huh? Hey, why’d you get passed over for that anyway?”

“Excuse me?” Underneath all his British properness, Oliver senses a touch of offense. “Passed over?”

“Yeah, you know, once Mr. Dennis retired, everyone figured the job was yours. But here you are. Still vice principal.” He flicks the nameplate on the pristine desk and thinks he sees an eye twitch.

“Not that it’s any of your business, but I declined the offer. I’m a few years short of early retirement and, believe it or not, Mr. Queen, I have ambitions that don’t involve the four walls of this institution.”

He doesn’t. Believe it, that is. Mr. Steele is such a fixture at Starling City Prep, he’s an institution in of himself. But whatever he needs to tell himself to deal with having some revolutionary upstart as his new boss, Oliver figures.

“So. What’s up?”

“I believe you and Mr. Diggle have come to an agreement, but I can’t have you skulking about the campus. Parents will complain, and it sends the wrong message.”

He shifts uncomfortably in the meant-to-be-uncomfortable chair. To be honest, this whole gambit was more than a little improvised. When he woke up this morning, he wasn’t planning on haunting his old school. Not until he found Raisa in the kitchen making sandwiches because “Miss Thea usually returns home for lunch.” The “and does  _not_  return to school” went unsaid, but it was the same exact shit he pulled in high school.

“Can’t you just pretend I’m Thea’s protection officer or something?”

“Aside from your being vastly underqualified for that position,  _no_. I would like you to vacate the premises immediately. Before more drastic measures must be taken.” The dismissal is curt, and Oliver’s thinking he shouldn’t have opened this conversation by trying to insult the old curmudgeon.

“Look, I think we’re getting off on the wrong foot. Or, you know, have always been on the wrong foot,” he mutters in acknowledgement of his high school days trying to torment the stalwart Mr. Steele. “I’m not doing this for kicks. I’m trying to help Thea before she turns into, well, me.”

“An admirable goal, indeed, Mr. Queen. In fact, we share the very same one. However, constant babysitting is not going to help matters. Have you tried  _talking_  to your sister?”

Oliver shifts again, sighing. “She doesn’t want to hear it.”

“That sounds familiar,” Mr. Steele mutters sarcastically before motioning for him to continue.

“She thinks just because I’m fucking around, living off my trust fund, that she should do the same thing. But she’s got way more to offer, and I don’t want her to regret not taking school seriously if it ends up biting her in the ass in the future.”  _Like me_ , he thinks.

“Again, we seem to be in agreement.” Oliver’s not sure he likes the way the vice principal is eying him speculatively. “I believe you’ve put Miss Queen off her escape artist tricks for today. I suggest you try speaking with her again at home, and I will call on her in the morning. I trust we won’t be repeating this conversation tomorrow, Mr. Queen. After all, there’s no such thing as improving your attendance record  _after_  graduation.”

Oliver flashes a wry grin at the unexpected wit of Mr. Steele’s dismissal this time around. He launches himself out of the ass-numbing chair—yeah, he’s definitely not eighteen anymore—and heads for the door. “Hey, one last question. What do you think of Dalton Fuller?”

The vice principal levels him with an assessing but long-suffering look. “Between two adults, Mr. Queen? You may be wasting your potential, but Mr. Fuller doesn’t have an ounce to begin with.” Oliver barks a short laugh. Apparently, he’s been underestimating his old nemesis this entire time. “It would greatly benefit Miss Queen if their association were to come to an end.”

“I think we’re going to get along just fine this time around, Mr. Steele.”

“Indeed,” his old pain-in-the-ass agrees with a raised eyebrow. “One last question for you as well. Have you met our new principal yet?”

 

* * *

 

Oliver loiters as long as he’ll risk it in the office. But he can flirt with the receptionist for only so long and he has zero desire to run into his old guidance counselor, who’s sure to be a condescending shit about how he hasn’t amounted to much. That means he doesn’t get a glimpse at the new principal despite how curious Mr. Steele’s leading question made him.

 

* * *

 

When the final bell rings, Oliver is leaning against his car, waiting. He’s a far cry from the dozens of hired drivers waiting for their charges to emerge, and there’s already a group of girls staring at him and gawking. He knows better than to engage, though. That’s a slippery slope.

Thea’s with some other kids when she does exit the main entrance but easily spotted by how the crowd practically parts for her.  _Moses and the Red Sea_ , he thinks, pulling out the reference from somewhere. When she sees him, Thea stops in her tracks, an incredulous and pissed off look on her face. For a second, he thinks she’s going to follow that confirmed waste-of-oxygen Dalton Fuller to his car, but she should know he won’t hesitate to give chase and bodily throw her into his car.

With a truly petulant stomp, Thea makes her way to him. Despite her theatrics, he can tell his presence is adding to her cool points. Not everyone gets picked up by their “Most Eligible Bachelor of Starling City”—suck it, Tommy—brother in his imported, and not entirely street legal, Pagani Huayra. He opens the passenger door when she’s a few steps away, and she smoothly slides in.

He waits until they’re a good distance from the school to break the awkward silence.

“I wasn’t always like this, you know. I had my shit together once upon a time.”

Thea’s only response is a disbelieving scoff.

“I did,” he insists with a chuckle. “Remember that summer I stayed in Boston? You were about ten. I signed up for summer classes. It was only three classes but I aced them. Mom and Dad got me a new car for it.”

Out of the corner of his eye, he sees Thea’s eye roll. “Is that why you did it?”

“No. The car was a surprise,” Oliver admits readily, “I did it because they threatened to cut me off if I didn’t stay at a school for longer than a semester on my own merit. So I... agreed to go to summer school, and they got me a tutor.”

“She”—Thea turns towards him in her first genuine sign of interest—”was the first person outside of our family to believe in me. She didn’t treat me like I was dumb. She expected me to be smart and hard-working and she expected me to meet that expectation. It was kind of powerful, you know. For the first time in my life, I accomplished something because I worked hard at it, not just because Mom and Dad bought it for me.”

“So what happened?” Thea prompts because she knows as well as anyone that that attitude didn’t last.

“We started dating. I thought that was the beginning of a new chapter in my life. But I came home at the end of summer to see you and Mom and Dad, and when I got back a couple weeks later, she had already moved on. So I left Boston and kind of just fell back into old habits. Mom and Dad were never actually going to cut me off, it turns out.”

Thea’s staring at him thoughtfully, and it’s kind of unnerving. “Were you in love with her?”

Oliver considers it for a moment. It would make a better story, but he doesn’t like lying to Thea about important things. “No, we were together only a few months. I liked her, though. More than I’d ever liked a girl before. It was a little crushing—”

“To be dumped?” she interjects with a knowing smile. “First time, huh? Must be why you’re still all fixated.” Yeah, a therapist would probably have a field day with his ego. That’s not news. “It’s dumb, you know. To change  _for_  a person and blame them when it doesn’t work out. Even the movies tell you that.”

Forget the therapist. His little sister will just take him apart in a few sentences.

“I don’t blame her for how I reacted,” Oliver corrects. Maybe he did back then, but he’s older and wiser now. “But I do regret  _how_  I reacted. She taught me a lot, and I should have used that to make myself a better person rather than throwing it all away because we didn’t work out. I don’t want you to have regrets like that.”

“I’m not near as bad as you, Ollie,” Thea scoffs dismissively.

“You’re not,” he agrees, although the possibility of  _yet_  gives him nightmares, “but that’s not exactly a high bar to clear. You’ve got so much potential, though. I don’t want to see you waste it, like I did with what little I had.”

Unexpectedly, Thea reaches across the center console to jerk him into an approximation of a hug. “You’re not as bad as you think, Ollie. You’re a pretty awesome big brother when you’re not stalking me at school.”

Awkwardly, he reaches to pat her shoulder before she settles back in her own seat. “I don’t want to babysit you like that either. But you’re old enough to know you shouldn’t keep blowing off school. Maybe you won’t ever use pre-calculus in real life, but the discipline of going and applying yourself matters. Why do you think I couldn’t ever make it through college?”

“No one ever held me accountable in high school. Mom and Dad paid my way into college. Then everyone’s surprised when I get there and have no idea how to go to class or study. Like I was going step foot on campus and magically transform into a responsible student who gives a fuck. And now I’ve got no prospects—even Dad doesn’t trust me to work at QC—and no ambitions. I’m an unemployed, complete waste of potential, and my only goal in life right now is to keep you from becoming the same.”

“Don’t you think you’re being a bit dramatic?”

“Thea, you don’t know how much I wish I could go back and do it all differently. I can’t so I guess I’m going to have to live vicariously through you.” Oliver treats her to a sarcastic grin, and she flops back against the seat.

 

* * *

 

The next morning, he’s knocking on her door with one hand, waffles in the other. “Rise and shine!” Her response is a hearty “Fuck off!”, but he doesn’t stop knocking.

During the next week, they settle into a routine. He wakes her up, shovels some breakfast into her complaining mouth, and drops her at school. Some combination of their talk and whatever Mr. Steele said to her works because she sits through her classes, and he picks her up at the end of the day.

Thea still doesn’t do her homework, and that’s fine for now. Baby steps, after all. She might just be waiting for him to get tired of this routine, but he won’t. Her scores on the next tests even creep up, a byproduct of her passive listening and more evidence of how well she would do if she just applied herself.

Oliver tries not to be this hovering, suffocating shadow. He doesn’t stop her from spending the afternoons and nights “hanging out” with her friends and doesn’t actually enforce her curfew. But he’s still there every morning to drag her to homeroom. Eventually, the exhaustion catches up with her—even her teenage energy can’t last forever—and she spends more weeknights at home with him and Raisa. Echoing Tommy, she also takes to calling him a boring hermit. He can live with it.

 

* * *

 

They’re three weeks into this arrangement when their parents call to say they still haven’t made return plans. With a grimace, he and Thea wish them well and assure them the house is still standing. Oliver doesn’t begrudge them the time away, and he’s not super psyched about continuing to play parent to Thea, but he can’t deny the new arrangements are working.

One afternoon, he wanders into the media room and finds Thea stuffing a book under the couch cushions upon his entrance. Normally, he would let her have her secrets, but this thing is thick. Like textbook-thick. Not exactly a romance novel, or a dirty rag like he was hiding back in the day. “Whatcha got there, Speedy?”

In true little sister fashion, she sticks her tongue out at him and mumbles, “Nunya business.”

He fishes the book out from between the cushions and frowns at the cover.  _The Ultimate Guide to Coding for Beginners_. Oliver sends her a confused look, because why was she hiding  _this_  from him?

“Dalton thinks it’s stupid.”

“ _Dalton_  is stupid,” is his automatic (juvenile) retort. Seriously, though. Fuck that kid.

Oliver flips through the book cursorily, but it’s not what really has his attention. He tries to tamp down his excitement at Thea maybe taking an interest in something school-related. “Computers, huh?”

“The new principal. She’s all about them. Calls coding a mystery to solve, which is kind of lame but you know...” she trails off with a self-conscious shrug.

“Thea, if you’re interested in this, you don’t need to apologize or make excuses,” Oliver says sternly. She rolls her eyes at the trite sentiment. “I’m serious. Coding is, like, the wave of the future or whatever, right? It can’t hurt for you to know the basics. God forbid, but one day you might actually have to support yourself with a job and everything. This would be a pretty good skill to have.”

Thea cracks a smile at his dramatics. “Let’s not jinx the family fortune.”

 

* * *

 

Oliver really wants to meet this new principal now. Shake her hand or something for getting Thea interested in something other than boys and partying, and for starting to open Thea’s eyes to what a self-righteous prick Dalton Fuller is.

The next morning after dropping Thea at the front, he loops around to park in one of the few visitor spaces. He’s not going to make an appointment or anything but he figures the principal can’t afford to turn away a “concerned parent.”

She’s the first female principal in probably ever and could use as much family buy-in as she can get. According to Mr. Steele, pre-retirement, Mr. Dennis stridently opposed the board hiring her—because of course the old coot did—and it’s left an impression on the parents. Honestly, he’s more than a little curious about the “nontraditional” hire turning the old guard on their heads.

The assistant greets him cheerily and informs him that, yes, the principal is in her office. With that, he breezes past her desk, ignoring her calling him back when she realizes he’s just going to waltz in there. 

Oliver knocks on the half-open door but pushes it open before he gets a response. He plasters on his most charming smile and just before the principal looks up, he’s struck by the oddest sense of déjà vu. His mouth dries as Felicity Smoak sends him a long-suffering look, probably in response to his lack of manners, and placidly says, “Hello, Oliver.”

 _He’s not the brightest crayon in the box, the sharpest knife in the drawer, the roundest cookie in the jar, or whatever dumb comparison exists. But he’s not_ stupid _. He knows tutoring is his best shot at surviving a college for more than a measly semester so his parents won’t disown his useless ass. That’s why he signed up for summer classes, of all depressing things, to show them he’s serious._

 _Still, Oliver’s not expecting the woman—_ girl _—in front of him when he shows up to his first session twenty minutes late._

_She’s young. Like so young she might be closer in age to Thea than him. Oliver thinks she must be one of those child geniuses with more IQ points than Facebook friends. She probably got shuffled off to college because she was too bored in high school and is now stuck tutoring spoiled brats for pocket money._

_This should be easy._

_Oliver plasters on his most charming smile and drops into the vacant seat across from her. Surprisingly, she isn’t flustered but fixes him with a tired look. She slides a page halfway across the table then speaks. “Look, I need the cash, and you need the grades. Let’s not make this harder than it needs to be.”_

_Leaning forward, he can see that the paper is really a schedule, an intense one given the small, cramped writing. He looks up at her with a disbelieving expression, but she’s unmoved. “Do we have a deal?”_

_With a grimace, he holds out his hand._ Just three months _, he thinks, as she shakes his hand._

_“Deal.”_

 

* * *

 

_“Felicity!”_

_If his yelling her name wasn’t drawing enough attention, his sprinting through the quad is definitely doing it. He catches up to her just as she turns around and he doesn’t hesitate to wrap her in a bear hug that carries them a few steps off the sidewalk and onto the grass. “We did it!”_

_“Yeah?” she questions with a laugh, already caught up in his excitement. “You passed?”_

_Oliver pulls back to grin in her face. It’s his first round of midterms since she began tutoring him, and he knows she’s nearly as invested in his improved performance as he is. His first test was just this morning, but the professor already emailed him his score, knowing and impressed with how much effort he’s put in._

_“Passed? I aced the damn thing,” he gloats, pleased when she throws her arms back around his neck._

_It’s as much her victory as it is his. Without Felicity, he would have never committed, never studied with any consistency, never gone to class. The girl genius he tried to dismiss that first day has become one of the most important people in his life._

_The friends she was walking with excuse themselves to the cafeteria, and he tries to feel bad. Felicity deserves normalcy, friends and a boyfriend. She deserves to relax, to be made to feel special, to not have to carry his sorry ass through his classes._

_The problem is his parents pay her for that last thing even as he desperately wants to be the person who helps her with the first two._

_Felicity’s not as young as he first suspected. He knows she turned eighteen last week because he helped her celebrate by dragging her out of the library and acquiring her a beer to try. (She very cutely grimaced at the taste and passed it back to him with a “thanks, but no thanks.”) Oliver’s a little older than he should be for how many college credits he has to his name but he’s still only twenty. As Tommy keeps reminding him, it’s all perfectly legal._

_Now that he knows he can do this school thing, maybe even without her help, it’s time to make a move._

_“Hey, Felicity?”_

_“Hey, Oliver?” she returns, still smiling._

_“Can I kiss you?”_

_For a moment, time stops. Then Felicity unfreezes and whacks his arm. “No!”_

_“No?” he repeats, helplessly. Because he sincerely thought there was something there. He doesn’t think Felicity hangs out with the other students she tutors, doesn’t help them pick out birthday presents for their moms, doesn’t listen to them drunkenly ramble at her in the middle of the night because he wants to tell her he likes her but he can’t work up the nerve so he talks about everything else that comes to mind. Apparently, he’s wrong._

_“I’ve had a massive crush on you for weeks now. You can’t just come up and ask if you can kiss me!” Oliver tilts his head, confused by her rejection and revelation. “You just have no idea how intimidating you are, do you?” Felicity asks, he guesses rhetorically, at a much more subdued volume._

_“Neither do you,” he retorts. There’s a reason he tried to call her Doogie in the early days. (It was kind of a defense mechanism. She immediately shot it down.) “So,” Oliver hedges, trying to get back on track, “can I kiss you?”_

_“What are you waiting for?”_

 

* * *

 

_Oliver’s whistling as he approaches Felicity’s new dorm building for the year. He has no idea how he’s going to get inside, but there’s probably some coed he can charm for access. Not that he’s interested. He hasn’t been interested in anyone but his girl genius for months now._

_He hadn’t even been that excited to go home in the weeks between the end of the summer session and the start of the fall semester. But his parents wanted him there to reward his good grades, and it had been too long since he’d last seen Thea. So he reluctantly agreed to leave for two weeks, something he felt even worse about in the days leading up to his departure._

_Yes, Felicity Smoak turned him into a sentimental sap about sex. So what? For awhile there, he thought he’d never get to kiss her, never mind have sex with her. He hadn’t been psyched about leaving her days after that happened._

_But Oliver’s going to make it up to her now. As a technical junior (she’s already finished her bachelor’s and is starting on her dual masters, but it’s her third year at the school), she finally got some priority in the dorm room lottery so he knows she’s got a single. He plans on taking every advantage of that before classes start up next week._

_He slips in the building when someone leaves. No charm necessary, just an over-the-shoulder “Thanks!” After jogging up to third floor, he knocks on the door and is greeted by some dude, shorter than him and dressed in all black and with a scowl on his face._

_Oliver recoils. He checks the room number again then goes back to the staring at the guy. He’s about to ask if he’s got the wrong room when Felicity ducks under the guy’s arm, pushing_ him _back into the room and trying to keep_  Oliver _out._

What the actual fuck?

_Apparently, Oliver’s not alone in his thinking because the stranger calls out, “Who the hell is this, babe?” Despite Felicity’s attempt to block him, Oliver works his way into the room to see him taking a seat at the desk, making himself comfortable._

_Babe?_

Babe?

_If anyone’s going to call Felicity Smoak by a pet name, it’s going to be him, Oliver Queen, her—_

_Okay, so they haven’t defined the relationship yet. But still, if anyone’s going to have first crack at babe—not that he would ever call her that—Oliver figures it ought to be him. He knows he’s somehow significant to her, this budding genius whose potential the world is still clueless about. If not her first, then he’s her first in a while. Oliver doesn’t think Felicity would take that lightly. He doesn’t mean that in a bad way. She’s just been a little shy and almost sweet, a contradiction to how she rides his ass in tutoring sessions._

_He looks to Felicity, waiting for her to tell off this Hot Topic reject, but she just flushes and stares at her shoes. “Cooper, this is Oliver.” No mention of their months of... whatever at all. When he thinks that’s it, that’s the lowest he could feel, Felicity continues, “He’s one of my tutoring students.”_

_Oliver can’t even hide the hurt in his expression. It’s a good thing this Cooper dick is already focused back on his laptop. Felicity won’t meet his eyes._

_“Well, get rid of the idiot, babe. We’re in the middle of something.”_

_With the wind knocked out of him, Oliver turns to the door, blindly grabbing the handle. He doesn’t see, and wouldn’t even care about, Felicity mouthing “Sorry” to him._

_Fuck this place._

 

* * *

 

“Wait!” 

She’s chasing him back towards the parking lot, moving faster in those heels than he would have suspected.

“Oliver, will you just—” He must surprise her when he stops next to his car, turning to her with an expectant look, because she finishes with a lame, “Wait?”

Oliver doesn’t speak while she catches her breath. There’s something comforting in seeing Felicity fidget in the same way she did in college. He still rubs his fingers together, as she once pointed out as his tell.

“Um, your parents have missed all of Thea’s parent-teacher conferences this year so far,” she says, and he rolls his eyes so hard he’s surprised they don’t fall out of his head.

“Are you fucking kidding me right now?”

Felicity straightens her glasses as she admonishes him. “Please don’t use foul language on campus.”

With a dark look, Oliver takes a step forward. He doesn’t mean to be menacing, but there are few other interpretations. Still, Felicity doesn’t back down. Very deliberately, he repeats, “Are you  _fucking_  kidding me?”

Self-consciously, she looks around the parking lot, as if someone’s going to catch them  _talking_ , and that’s when he loses his patience. Oliver jumps into his car and leaves her there.

 


	2. Chapter 2

Of course Thea’s easy reformation is too good to be true.  

One day he gets a call from the police station, telling him to pick up his sister. When he rushes down there, Thea’s sitting at a desk in the bullpen. She looks so small, playing with her bracelet and scuffing her sneakers on the linoleum floor.

Laurel is quick to intercept him before he reaches her. His ex-girlfriend but still friend manhandles him down the hall and into an empty interrogation room. He knows they’ve caused a scene because Thea’s head had whipped up and she smothered a smile at their antics.

When he gets his bearings, Oliver realizes he’s not in the interrogation room but the one adjacent to it. Huh. He’s never been on this side of the mirror before.

“Thea’s fine.” He opens his mouth, but Laurel holds up a hand. “Stop. She’s  _fine_.”

God, no wonder they didn’t last. After an exaggerated eye roll, he grumbles, “Then what happened?”

“She was in the Glades.” Then it’s Laurel’s turn to roll her eyes at his reaction. “Don’t ask me. That’s a conversation you need to have with her. Some kid pulled a snatch and grab with her purse. Thea and her friend chased after him, and conveniently, they ended up in front of CNRI where Lieutenant Drake happened to be dropping off some files.” Oliver lets out a disbelieving chuckle at Thea’s luck. “It was stupid to chase after him like that—he could have had a weapon—but she’s fine.”

“Yeah, except for the part where she’s hanging out in the Glades. I want to talk to this punk.”

“Get in line. Thea’s already chomping at the bit.” His  _hell no_  expression must be obvious because Laurel counters with, “Actually I think it might be good for her. She could do with a reality check. And it’s probably going to be super entertaining.”

Oliver has no doubt. Thea takes her purses seriously. She’s probably going to rip the guy a new one for trying to separate her from one. 

“That him?” he asks, suddenly taking note of the person in the actual interrogation room on the other side of the mirror.

The kid’s wearing a baggy red hoodie and handcuffed to the table, which seems excessive for a snatch and grab. He’s gaunt, cheekbones and jaw line sharper than they should be. The defiant look on his face is expected, but Oliver thinks he might be a little scared, too. Definitely hungry. He can imagine why Thea and her designer outfit were an appealing target.

“Roy Harper, nineteen. Born and raised in the Glades so, you know, already well on his way to a career as a petty criminal.”

Oliver cringes but nods. “Any chance of leniency?”

“They’ll ask, but he’s a repeat offender,” Laurel shakes her head with something like resignation.

“Drugs?” is his next question.

“Nothing on his record at least. A couple MIPs for alcohol.”

“Violent crimes?”

“Seems to know enough to avoid aggravated charges because he’s never used a weapon. Been picked up a couple times for fights but he’s always claimed self-defense. The girls sometimes come back to corroborate.” Oliver must look confused because she continues, “Apparently, he’s got a bad habit of trying to fight off guys—bigger, stronger guys—attacking women.” Laurel gives him a sidelong look. “You feeling sorry for this kid?”

Oliver takes a moment to respond, but yeah kind of. “Come on, he’s not like me or Tommy. He didn’t do this shit because he thought it was funny or to impress a girl. He’s probably just hungry or something.” He imagines the cost of one of Thea’s purses could feed a family for a month.

“Which is why I think Thea should talk to him,” she points out. “Yeah, he broke the law and committed a crime. Yeah, he’s kind of made her a victim, although she can reject that mindset. But they’re barely two years apart, and he’s got some sort of moral compass. Circumstances are really all that separate them. In another situation, another family, who knows how he would have turned out?”

 

* * *

 

Oliver watches as first Lieutenant Drake then Thea enters the interrogation room. After his and Laurel’s chat, Thea was relieved to see him finally, didn’t even protest the tight hug he wrapped her in. She was surprised when he agreed to letting her speak to her assailant on the condition that he’d be watching from the other side.

_He’s_  surprised Captain Lance is letting this happen. Despite him and Laurel and Sara all getting over their high school cheating scandal to stay friends, the captain still holds a grudge against him for it. But, thanks to Sara, the captain also holds a soft spot for younger daughters with something to prove and has always had a kind smile for Thea. Then again, maybe no one actually asked his permission.

Because this whole setup? Even with the punk handcuffed to the table? Seems like a real bad idea.

“What the fuck do you want, princess?”

Oliver’s not expecting anything different, but it still makes him angry to hear Thea talked to like that.

Instead of answering, Thea asks in her snottiest tone, “Do you know who I am?”

“Yeah,” he returns defiantly. “Why d’you think I stole your purse? Rich girl like you ain’t carrying around a knockoff.”

“Why’d you do it?”

“You deaf? Or can’t you hear me up in your ivory tower? I just told you.”

Oliver has to give the kid points for being quick on his feet. He’s obviously not easily intimidated either, even with Lieutenant Drake glaring at him from the corner of the room.

“Why didn’t you just ask for some money?” Thea tries again.

Roy scoffs. “I don’t do handouts.”

“Well, now, you get to do jail,” Thea snarks right back. Roy doesn’t like the reminder much because he snarls at her and looks away. “Look, I didn’t mean it like that. To rub your face in it, I mean.”

She sighs and looks at the mirror—at him—at a loss. “Wasn’t there something else you could have done? You don’t need to steal.”

“Says the girl born with a solid gold spoon stuck up her ass. You think I have options? Here are my options: steal shit, or starve and die. If you can think of something else, feel free to drop it in the suggestion box on your way out.”

Thea’s fed up. She pushes off the wall she’s been leaning against and exits the room. Oliver’s quick to meet her in the hall where she stands, visibly shaken. Laurel’s there, too, watching carefully yet sympathetically.

“You okay?” he asks, running his hands down her arms.

“Yeah,” she pauses and closes her eyes, “Let’s just go.”

“You haven’t finished giving your statement yet,” Lieutenant Drake reminds her from where she’s closing the door to the interrogation room.

Thea looks at him while she says, “I’m not going to. We’re not pressing charges.”

Laurel gently cuts in with, “The DA might still—”

“I won’t testify either,” Thea interrupts. “I’ll be—what do you call it?—a hostile witness? Look, it’s just— It’s a bad thing that happened, but I’m fine and I still have my purse. And he— He’s still going to go hungry tonight because now you don’t have a reason to keep him locked up here long enough for a meal. So we’re all back where we started, I guess. Let’s  _go_ , Ollie.”

Oliver shrugs apologetically at the women then follows her down the hall.

 

* * *

 

“You knew I’d feel bad for him. That’s why you agreed to let me talk to him,” Thea accuses once they’re on their way home.

He hums in acknowledgement.

“Mom and Dad would have had him rotting in jail,” she continues almost to herself. “He shouldn’t have stolen my purse. But he shouldn’t have to steal to eat.”

Oliver feels bad. They made this kid into a pawn for the purpose of teaching Thea to recognize her privilege. At least it seems to have worked.

 

* * *

 

One day, he finds the coding textbook laying behind the couch, seemingly forgotten. He asks Thea what’s going on, and she replies with a blasé, “Eh, not for me.”

“That’s okay. You’ll find something else,” he says because it was probably what he needed to hear and never did.

A week later, she digs out the fancy digital camera she got for her last birthday and tells him she’s signed up for a photography elective. The week after that, she comes home with a large sketchbook for her fashion sketches.

He remembers being approached at the mall or downtown by talent scouts interested in recruiting his sister for modeling. Mom always walked away from them, no matter how legitimate they were. Something about modeling being too “common” for their family pedigree.

Oliver’s nothing but encouraging with every idea.

Try, try, try again. 

 

* * *

 

Oliver can’t believe he’s twenty-seven and attending a high school basketball game. Thea asked him to drive her because she’s still wary around Dalton ever since she broke up with him. She doesn’t think he’ll do anything other than be passive-aggressive and make her uncomfortable, but Oliver doesn’t trust the little shit.

He sits at the top of the bleachers, so Thea can’t complain he’s hovering but he can still keep an eye on her and her friends, and wonders what the hell’s happened to his life.

Felicity’s there. Earlier, he saw her running one of the registers at the concession stand. Probably calculating people’s totals and change faster than humanly possible with all those tricks she tried to teach him forever ago. So he shouldn’t be surprised to see her climbing the stairs after halftime. Every few rows, she stops to chat with parents or students, but it’s clear she has a destination in mind.

_Him._

Silently, Felicity settles next to him on the bench. She’s not touching him, but he can feel the weight of her presence anyway. “You never let me explain that day. You just left and then you left town.”

He doesn’t want to do her the favor of a response, but the scoff slips out anyway. “You’re telling me that you, Felicity Smoak, technological savant, couldn’t find a way to get in touch with me?”

She makes a disbelieving sound, caught in her lie, then continues, “I thought it would be best for both of us if I just left you alone.”

“Makes sense. You weren’t the one being cheated on and getting dumped without an explanation.”

“I didn’t cheat on you!” The exclamation comes out louder than she must intend because she slaps a hand over her mouth. Up here near the rafters, the sounds of the crowd and the game echo and bounce around. Thankfully, it’s also pretty deserted, leaving them with more privacy than expected for such a public place.

“I didn’t,” she insists more quietly. “Do you remember Dr. Wells?” How could he forget her mentor who she almost never shut up about? “He thought Cooper was up to something illegal, but he didn’t want to get the administration involved if it was nothing. So he asked if I knew anything. I pretended to help Cooper so he would let me in on what he was doing. All that “babe” stuff was just him being a presumptuous dick.”

After all these years, it shouldn’t matter, but the knowledge still eases the hurt left in his heart. Thea was right, he’s always carried a little baggage over them because it was the first time he was on the receiving end of such callous behavior. Obviously, it’s stayed with Felicity, too, if she remembers little details like being called babe.

“Did you,” he asks out of sheer curiosity, “figure out what he was up to?

“Yeah, he was trying to erase all the student debt in the Department of Education’s system. Trust me, I’d be more than happy if my debt just disappeared, and I don’t even have as much as other people because of my scholarships. Unfortunately, crippling students with massive debt is now a cornerstone of the American economy. It would have been chaos, caused another recession or worse.”

Felicity breezes through the explanation as if it’s nothing. As if she didn’t help prevent an economic crisis. He’d jokingly referred to her as “girl genius” on multiple occasions to her never-ending embarrassment, but apparently the name holds up.

She shifts towards him suddenly, trying to catch his eye, and Oliver knows this next part is really what she came to say. 

“I was younger than you, less experienced than you. Our life experiences were already  _so_  different. And it’s not like your usual types were around during summer school. I figured I was destined to be a fling so when you saw Cooper and jumped to conclusions, I let you. Because, between the two of us, if anyone was going to do the heartbreaking, it was always going to be you. I thought I was doing myself a favor, sparing future me a lot of grief. I knew that if I grew to like you anymore than I already did, I would be devastated when you eventually got tired of me and left.”

Oliver can’t fault her logic. His track record spoke for itself. Felicity was always a little hesitant with him, and now he knows why. She thought—thinks—his interest in her wasn’t genuine or sincere enough to last very long. To be honest, he doesn’t know that they would have been together long, whether he, and she, would have been mature enough for that type of relationship, but still—

“I really liked you,” he admits quietly. Felicity turns surprised eyes his way. “I even told Thea that. That I’d never liked a girl as much as I liked you.”

“I really liked you, too. How could I not? You just swaggered in with your good looks and dumb hair and weird charm that really shouldn’t have worked. I tried so hard to keep it from working, but we were spending so much time together, and everything was so simple and easy between us. When you went back to Starling City, it was like— It was like you took the rose-colored glasses with you. Reality crashed back in. I figured it was the same for you.”

After letting his first instinct to protest simmer down, Oliver can see it from her side. He was always aware of Felicity’s inexperience compared to his, her lack of social life, the awkwardness that came with being younger and still so much smarter than her peers. He just didn’t know that she viewed it all as such a handicap. Somehow, he finds himself wanting to reassure her. “It wasn’t. I was excited to get back, to see you again. Then I just felt like such a sucker. I remember waiting for you to do something, say something, explain exactly what you just did about Wells, but you didn’t. You called me your student. It was like you were ashamed of me.”

“No,” Felicity shakes her head in denial, “I didn’t tell him you were my boyfriend because I didn’t know if I had the right to—we never talked about it—but also because he was already so angry at society and the  _hierarchy_. If he knew your last name or how rich your family is, he might have targeted you, too. I didn’t want to put you on his radar like that. Better to let him think you were just a paycheck.”

He considers his options. He could yell at her for letting him believe the worst for all these years. But he meant what he said to Thea in the car that day. He doesn’t hate Felicity anymore for, essentially, giving him a taste of his own medicine. Plus, they’re in a _high school_ gym, not just hers but also his little sister’s. Thea’s paying more attention to them than she’s letting on, and he knows she’ll never forgive him if he causes a scene and embarrasses her in front of everyone. 

After a long silence, he mutters bitterly, “Would have been nice to know that before now.” Felicity hums in uneasy agreement. “So what now? It’s all in the past, and we’re adults. How do you want to do this?”

If Felicity’s surprised that he’s trying his hand at maturity, she doesn’t let it show. “Does Thea need to know about us?”

“She’s been staring at us for the last five minutes so I think she’s going to have questions,” he answers calmly. Felicity nearly jumps in her seat. When she scans the crowd to find Thea, Oliver offers his sister a sarcastic wave. Thea doesn’t wave back, giving him her back again but somehow with attitude. “I don’t want our past to affect her at school.”

“Me neither,” she agrees immediately. “You said you told her how much you liked me?” Felicity still sounds incredulous about that, and he’s starting to get offended.

“A girl I dated back in college. I didn’t use your name,” he explains with a slight glare. This time, she shrugs it off with a sheepish smile. “How about you’re up here lecturing me about missing parent-teacher conferences and we just go back to our normal lives? No one has to know anything.”

He’s definitely offended by how quickly Felicity agrees to the plan. With barely even a goodbye, she heads back down the bleachers. For the rest of the game, Oliver pretends not to see Thea sneaking questioning peeks at him or to track Felicity as she glad-hands her way around.

 

* * *

 

It’s been two months, and their parents  _still_  aren’t home. They call every week from some new and exotic location and dodge the question of when they’re coming back. His dad’s still remotely running the company—Oliver only knows this because of the lack of headlines worrying about a QC bankruptcy or buyout—and his mom’s still figuring out how to trust his dad.

So he and Thea settle into their new normal.

Oliver doesn’t mind it much. He kind of likes having a routine. Every day, it’s: have breakfast with Thea and Raisa; drive Thea to school; wave to Mr. Diggle, the security officer, who’s less rent-a-cop and more former Army sergeant because Starling City Prep has some  _rich_  kids wandering around; kill time with a run and/or the gym; shower; lunch with Tommy or Laurel or Sara or whoever’s available really; shoot the breeze with Mr. Steele who’s stealthily hilarious; and wait for Thea to get in the car. Sometimes, he looks for a certain blonde ponytail among the crowd, but he never does see the right one.

This week is different. He’s finally been browbeaten into going to those parent-teacher conferences his parents couldn’t even bother to show up for. It’s almost a good thing that they’ve been put off because he gets to hear about how much Thea’s improved recently. The teachers don’t bother talking about college prospects—they know his family will get her into her school of choice—but he reads between their lines. Unlike him, Thea might actually earn her diploma this last semester. 

When he gets home after the third straight afternoon of conferences, he’s surprised to hear the TV on in the media room. Last week, he gave Thea keys to one of the Audis, and she hasn’t abused the privilege so far but she also usually goes out between school and dinner. 

“Hey, Ollie,” Thea chirps brightly at him when he enters the room, “This is my friend Roy. Roy, this is my older brother, Oliver.”

Oliver freezes in the act of scratching his ear. He stares at the kid like he’ll somehow transform into an entirely different person. After blinking multiple times, it doesn’t happen. That’s still the same kid who unsuccessfully mugged Thea.

What the fuck?

It’s one thing to not have him prosecuted and thrown into jail for essentially falling victim to the circumstances he’d been born into, but it’s another to bring him home like nothing ever happened.

This Roy watches him warily. He’s not stupid enough to think Oliver doesn’t know exactly who he is and he’s waiting for Oliver’s reaction to figure out if he should make a run for it or not. Oliver’s not even sure what he’s supposed to do.

“Roy, is it?” he repeats mechanically, and the kid nods stiffly. “Welcome to our home. Are you staying for dinner?”

“If that’s okay,” Thea answers for him. Apparently, her strategy doesn’t entirely consist of bulldozing past him and acting like this is all perfectly normal.

Oliver blinks, tries to shore up his defenses against his sister’s puppy dog eyes, and fails. “Of course,” he says tightly. “You let Raisa know already?” Thea nods in confirmation, and he finds a seat in an armchair. Just barely he avoids making a crack about counting the silverware because he knows that’s unfair. At least the teenagers keep a respectable distance apart on the couch as they all pretend to watch some Netflix show, so that’s one less thing for him to have a heart attack over.

 

* * *

 

“When I said you could do better than Dalton Fuller, I didn’t mean go befriend the common criminal who tried to steal from you,” Oliver moans after he gets back from dropping Roy off near his house. The kid wouldn’t tell him exactly where he lived, and Oliver knows that’s both suspicious and common sense of him.

“It’s not like that,” Thea grouses, throwing him a dirty look.

“Not like what?”

“Pity or charity or whatever. Roy’s smart, unconventionally sure, but still. And he’s actually nice. He also probably could have been an Abercrombie model in another life.”

Oliver’s annoyed that he can’t argue with any of those points. Roy made it a point not to go into any rooms without him or Thea, as if guarding against future accusations of theft. He was also almost excessively polite to Raisa, which is about the fastest way to score points with either of the Queen siblings. And, no, the kid’s not unfortunate looking, even though he probably grew up a little malnourished.

“How did you even run into him again?” Oliver asks suspiciously. “You’re not hanging out in the Glades for shits and giggles again, are you?”

Thea glares. “No, dummy. I asked Laurel if there was any way she could hire him for odd jobs or something at CNRI.” Oliver has to acknowledge that’s smart. With his rap sheet, it’s unlikely Roy could get a traditional job, not even at a convenience store or anywhere else. “She found some stuff he could help with and got his address off the system, and I went to drop it off in the suggestion box.”

Despite Thea’s lightheartedness, remembering Roy’s quip from their conversation in a police interrogation room doesn’t make him feel better. Oliver hums skeptically, and Thea immediately mounts a defense. “Hey, he showed up for work, okay? It’s only a part-time thing but it shows that when there’s another option, he’s willing to take it.”

“Fair enough,” Oliver finally agrees. He’s not in any place to judge someone’s attempts to make a better life for themselves, not when he was “born with a gold spoon stuck up his ass”. But he does need to ask Laurel if CNRI actually has funds to pay Roy or if she’s paying him out of her own meager salary. If it’s the latter, the Queen family should tack on another anonymous donation to the nonprofit. Actually, they probably should regardless of the answer.

“Be careful with him,” he warns anyway because Thea’s still his little sister and Roy’s still a boy.

“I always am,” she returns with a wink.

Oliver makes a mental note to see if Mr. Diggle knows any place that teaches self-defense to teenage girls.

 

* * *

 

Thea manages to convince Roy to attend prom with her. Without asking, Oliver knows Roy never experienced his own. Somehow, he’s tasked with taking Roy to the mall and finding him a suit that’s affordable and well-fitting.

Honestly, it’s not so bad. Suit shopping is one of the things he’s good at, and the kid fits off the rack pretty well, aside from needing the pants and sleeves hemmed. It’s not as uncomfortable as the first dinner because once Oliver asks him about CNRI, Roy actually has something to say.

He likes it. The clients are sometimes people he knows so he feels like he’s helping the community for once. Laurel’s a good boss, strict but still fair. She doesn’t lower her expectations for him, and when he’s done a good job, she tells him so and gives him more responsibilities.

The talking stops when Roy sees the price tags. They’re not anywhere fancy, but Oliver should have known better. A couple months ago, this kid was fencing stolen goods to buy food. The CNRI job is just part-time, and he’s probably living on a shoestring to avoid falling back into crime.

Oliver cringes. He can’t offer to pay. Roy has too much pride for that, and he doesn’t want to offend him. But he also doesn’t want to pressure him into overspending, stretching himself too thin, and undoing his progress.

Before the store clerk can come back to check in on them, Oliver lights on an idea. “So now that you know your sizes in a couple brands, Thea can do her online shopping thing and find all the sales. If we leave now, we can catch the Huskies game.”

Roy exhales a sigh of relief. He grabs onto the suggestion and neatly replaces the items with more care than Oliver expects. “Yeah, that’s a good idea. Let’s go.”

 

* * *

 

While he’s still riding the high of averting one crisis for Thea’s perfect prom, another comes crashing in.

Thea slams his car door shut so hard, Oliver winces. The gull-wing doors are notoriously sensitive, and she _knows_ that. If she breaks the damn thing, he’s going to find a way to actually ground her. He’s about to complain at her when he catches sight of the look on her face.

Thea’s  _furious_.

Oliver even hesitates as he carefully asks, “Are you going to tell me or—”

“Roy can’t come to prom.”

“What?” he questions because he just spent an afternoon at the mall with him. “Did you guys break up?” It’s the only explanation that makes sense to him.

“No! Roy is  _banned_  from prom!” Thea rants. “They say it’s because he’s not a student, but that’s a  _lie_. Last year, a bunch of people had dates from other schools. You know why? Because no one had to announce who they were bringing ahead of time! They’re just making this shit up because they don’t want someone from the Glades there!”

“Okay, calm down,” Oliver tries because that can’t be the rationale. Maybe they changed the rules about students from other schools. “I’ll talk to someone, and we’ll get this figured out. There’s no good reason you can’t bring Roy as your date.”

 

* * *

 

That thing in the TV shows where doctors get yelled at because they make promises they can’t keep? Turns out it’s a problem for normal people, too. Like Oliver who’s getting the sinking suspicion that, despite his best efforts, Thea’s perfect prom really is ruined.

“What? What is the damn issue? Is it because he’s older? Roy’s nineteen to Thea’s seventeen. Don’t get me wrong. I don’t love that he’s older. I don’t love that she has a boyfriend at all. But two years is hardly  _inappropriate_. We had the same age diff—”

He cuts himself off as the flush spreads across Felicity’s cheeks.

“Carrie Cutter wanted to bring a thirty-year-old man as her date to a  _high school_  prom. That was statutory rape, which is an entirely different scenario than Thea and Roy,” he finishes succinctly but heatedly. There’s a lot he doesn’t love about Roy’s past, but the kid hasn’t done anything  _that_  wrong.

Felicity cringes at the strange but true scenario that lead the school board to implement an age restriction on students’ dates. “I agree entirely,” she admits reluctantly, “Roy’s age isn’t the issue here.”

“It’s ‘cause he’s from the Glades, isn’t it?” Oliver finally sighs, rubbing at his eyes tiredly. “Come on, you can’t judge him for that. He’s working for a nonprofit legal organization and he’s really making the most of it. He’s doing the best he can with the opportunity he has.”

“I know.” Surprisingly, Felicity sounds as annoyed as he feels. “But his criminal history is too well-known, Oliver. Thea’s friends— They’re not as forgiving as she is. Once they found out who she was taking, they must have told their parents because I’ve already had multiple phone calls demanding that he be banned. I’m sorry but Thea can’t bring Roy to prom.”

“This isn’t fair,” he complains bluntly.

Felicity nods. “I know. And I wish things were different, but this isn’t Sara Lance bringing a girl as her date. There isn’t a community rallying around kids from the bad side of town to have a normal high school experience.”

“Can’t we just compromise?”

“How?” she asks tiredly. Oliver gets the feeling she’s already racked her brain trying to come up with a solution. And if Felicity Smoak can’t figure out a solution, what hope does he have?

“I don’t know. How about you ban all the students who should have a criminal record but whose mommies and daddies bribed the cops to make it go away?” He ignores her warning “ _Oliver_ ”. “At least then it would be fair. That’s what this institution’s all about, right? There’s no way people are buying their kids a rigged playing field, huh?”

Felicity’s not even trying to hide her amusement with his temper tantrum when she remarks, “You know, hypothetically, you would have been one of those banned students.”

“I know,” he admits grudgingly, “but just because I got a pass doesn’t mean people should continue to get a pass. And just because Roy couldn’t afford a pass doesn’t mean he should continue to be punished when he’s trying to do better.”

Oliver waits a second then pushes out of the chair. “You’re right. Other people aren’t as forgiving as Thea. It’s a damn shame.”

 

* * *

 

“I’m sorry,” Oliver apologizes the moment he gets home.

Thea’s more angry than disappointed, and he can tell Roy’s even angrier. No, Roy doesn’t really care about this prom. He only agreed to go to make Thea happy, which is something Oliver fully supports as someone invested in Thea’s happiness. But it’s just one more thing exacerbating the differences between him and Thea, one more way for society to exclude him and deem him unworthy.

Oliver doesn’t blame him for running out of the house. He doesn’t stop Thea from going after him, either.

 

* * *

 

“Oliver Queen, prom chaperone. Is the world ending?”

A smile turns up his lips so he swings away from Felicity and her teasing voice to hide it. “I heard you were short a chaperone. It’s the least I could do after you committed political suicide so my sister could bring her boyfriend.”

Felicity waves a dismissive hand. “It was the right thing to do, and suicide’s a strong word. Especially after a police captain publicly backs your play. Hard to badmouth someone who inspired a city-wide initiative to create more second chances for young offenders, all because she let one kid into a prom.”

“But at the risk of the children’s safety, Principal Smoak. How could you endanger them like that? You’re exposing all these innocent angels to a hardened criminal,” Oliver deadpans, mimicking the arguments that have been playing out on Starling City’s local public broadcasting station.  _Starling City Today!_ , more like  _Starling City Wouldn’t-It-Be-Better-if-It-Were-Still-the-1950s!_

“Oh, please,” she dismisses again, “He’s a nonviolent offender with a penchant for trying to stop violence against women. Roy’s rough around the edges but he’s kind of a marshmallow who’s totally gone for your sister.” Oliver sends her a questioning look, and she explains, “Thea brought him by my office last week to say thank you. They’re really sweet together. I can see why you like him.”

“I don’t like him,” Oliver issues the automatic denial.

“No, you just passionately argued for why he should be allowed to attend this prom because you think he’s as worthless as Dalton Fuller,” she sarcastically retorts. Her voice drops low at the end, in case anyone overhears her speaking ill of a student.

Oliver glosses over the entirely accurate description of their argument in her office. “I never said that I don’t like Dalton.” He knows that outward disapproval would have incentivized Thea to date the dunce for longer than she actually did.

“You didn’t have to,” Felicity graces him with a knowing smile. “Your rivalry with Max Fuller is actual legend at the school. And you almost hip-checked Dalton into the punch bowl fifteen minutes ago.”

And he’s a little annoyed the shithead managed to regain his balance without ending up with the spiked punch all over himself. Still, there are more important things to concentrate on. “You been watching me, Principal Smoak?”

“Maybe,” her voice lilts in a way that’s edging towards flirty.

Oliver doesn’t hate it. In fact, he extends a hand and waits.

Felicity smiles at the gesture but she hesitates. “I thought we weren’t supposed to know each other.”

“True,” he agrees, a little disheartened by her response. “This could be a getting-to-know-you dance?”

“How about a getting-to-know-you- _again_  dance?” she offers instead, finally taking his hand.

Her touch feels just as good as before, better even. With her hand in his and her eyes on his, Oliver struggles to remember the appropriate amount of distance to keep at a high school dance. He doesn’t even notice the looks and whispers they earn from students and chaperones.

 

* * *

 

“What now?” he asks when Thea climbs into his car with a stone-faced expression.

“Are you fucking my principal?”

Oliver chokes on his own spit at the blunt question. Rolling her eyes, Thea pounds on his back until he regains his composure and pushes her off. “Excuse me?”

“You heard me,” she doesn’t forfeit an inch, “Are. You. Fuc—”

“Hey! Language!” he complains, feeling so much like their mother. Thea rolls her eyes again. “No. I’m not dating or... romantically involved with Ms. Smoak.”

“Romance has nothing to do with fuc—”

“Stop it. I  _will_  ground you somehow,” is his threat. They both know it’s empty. He basically had to annoy her into becoming a mediocre student.

“Seriously. I’m sick and tired of hearing all this rumor and innuendo about you and Ms. Smoak. What is going on?” Thea sincerely asks.

And because she was sincere, Oliver will grant her a vague answer. “Nothing is going on. Is this because we danced at the prom?”

“Yeah. You know, eligible bachelor older brothers don’t normally chaperone school dances. And if they do, they don’t dance with the young, hot, unmarried principal without trying to get into her pants. But I know you didn’t because you insisted on driving Roy to his place and then us home. So what gives, Ollie? Don’t try to feed me that  _nothing_  lie again.”

“We were just talking about you and Roy. And what it might have cost her to lift his prom ban.” He knows it’s a successful redirect because Thea crosses her arms and gets that mulish look on her face.

“It was the right thing to do,” she insists stubbornly.

“The right thing isn’t always the popular thing,” Oliver reminds her. “I was just thanking her for taking a stand and telling her how much you appreciated it. A dance seemed appropriate. It wasn’t a big deal.”

Suddenly, Thea gets a wicked look in her eyes. “Maybe it should be a big deal.”

Oliver doesn’t hold back his groan. God help them all if Thea’s deciding to play matchmaker.

 


	3. Chapter 3

**Notes for the Chapter:**

> Sorry for the lagtime. Been on a road trip best described as a series of unfortunate events. (“But did you die?” ask my (asshole) friends.)

Oliver’s not really sure how he got to this point—wanting to reconnect with his ex-girlfriend, who was never explicitly his girlfriend and whom he harbored a bitter resentment towards for many years—but after the dance, he can’t stop thinking about her. God, if that’s not the most high school thing that’s happened to him in the past decade.

But it’s not like he can ask Thea for Felicity’s number, or even ask Felicity for her number. She was all too eager to walk away from him at that basketball game, and at the dance? Felicity made sure to keep her distance after they danced together, once they became aware of all the kids and other chaperones watching them. Still, he felt her eyes on him for the rest of the night, even caught her looking a time or two.

And ever since the dance, he’s seen Felicity out and about during the drop off and pick up times. Not every day, but often enough. She seems to know most of the drivers by name so he cottons onto the fact that she’s been avoiding the routine ever since he showed his face at the school. Whenever they do see each other, she offers the slightest wave and smile that he returns with the cool-guy-nod he perfected back in sophomore year. The simple interaction is enough to keep his interest, and Thea’s teasing, alive. Still, not even Thea’s teasing, can detract from the increasingly palpable _promise_ in their short exchanges.

Now all he needs to do is figure out how to capitalize on that promise.

His phone beeps, and he groans. Tommy needs to let up on the going out thing. Just because he and Laurel are “on a break” doesn’t mean Tommy can revert back to college behavior. He’s never going to convince Laurel he’s a matured adult with that shit.

But, no, the text is from an unknown number. Oliver straightens a little before he taps on the preview.

_Hi! It’s Felicity. I low-tech hacked your number by looking up Thea’s emergency contact info. Sorry for the invasion of privacy. Just thought you might want mine. :)_

Oliver can’t believe he’s getting excited over a smiley face. But that’s flirting, right? Damn it, where’s Thea when he needs her? Never mind. He can’t tell her about any of this anyway.

He leans back, trying to think of a witty reply. Texting wasn’t exactly a thing back when they were in college, and he’s rusty on this form of communication that doesn’t really allow for tone. Whatever he sends needs to be intriguing but not too eager but not dismissive. They’ve got a lot of catching up to do after all.

 

* * *

 

Oliver leans back against the railing, resting both elbows on top of the second bar and his head against the fourth. It’s a position he mastered a decade ago, and even back then the metal dug uncomfortably into his spine. A few rows below him is a rowdy cheering section, packed into the bleachers to get a better view as the soccer game wears on.

Thea’s down there somewhere, Roy conspicuously missing from the high school shenanigans. Which is why he’s here. For continuing protection against the judgmental and unfair stares of students, and mainly parents, who can’t get over their prejudices.

In any case, it’s strange to be back here. At once, eminently comfortable on his old field, yet decidedly  _un_ comfortable with the feeling and perception that he peaked in high school. He can’t help but reminisce on the good old days when life’s problems were laughably simple.

Sighing heavily, he lets his eyes wander around the field to the simple wood scoreboard with a fresh coat of paint. His eyes catch on a dejected-looking freshman sitting on the catwalk, loosely holding a pile of numbers, and swinging his gangly legs above the sign with Oliver’s retired number. His last name is on the side of the tallest building in Starling City, but that number is by far the only accomplishment he’s ever  _earned_.

The final whistle blows, signaling the end of the game, and the crowd erupts into cheers for the victorious home team. Oliver catches sight of Thea heading down to the sidelines with a group of friends. Unlike the old days, he’s content to linger on the bleachers while Thea finishes her goodbyes.

“Hey!” Oliver startles at the sudden yell, his eyes flying open when he jerks upright from his reclining position and skims his forehead against the bar. “Oh shit!” He’s too busy rubbing at his forehead for the sound of heels on shaky metal to really register, so he’s surprised when a soft hand wraps around his wrist, pulling his hand away to inspect the damage. “I’m sorry! Are you okay?” 

Smoothing out the wince on his face, Oliver mutters, “I’m fine. I was just surprised.” 

Her hand is still holding onto his wrist, and she’s, hopefully unconsciously, rubbing her thumb against the tendons on the inside of his wrist. Sparks shoot across his skin from the simple contact. God, is he really so hard up that a random stranger is having an effect on him? Awkwardly, he pulls his hand away, sighing at the repeated apology. Finally, he deigns to look at her and jerks back against the railing. 

_Oh._  

Internally, his high school self grimaces at how terrible his luck has gotten.

Felicity’s gorgeous even with her expression frozen in an embarrassed wince. “Are you really okay?” she questions sincerely, hand reaching for his head before she pulls it back. “I didn’t mean to startle you.”

“ _Felicity_ , I’m fine.”

They exchange a look at his saying her name. Oliver resists the urge to duck his head because it’s been too long since he’s actually said it. Despite their increasingly frequent texting, they haven’t graduated to actual phone calls. And now that he’s recovered from the unfortunate accident, he’s surprised that she’s approached him in public like this.

“What are you doing here?” The volume and tone of his voice is more questioning, letting her know he doesn’t mean it harshly. “Isn’t this bad for your reputation?” That comes out teasing and sly, and she shoots him a sarcastic look.

“No one’s really here to pay attention to us,” she points out, gesturing to the pretty empty field below. There are some people cleaning up, but the teams and other students have disappeared. Hopefully, Thea’s out in the parking lot, waiting for him still. “I just wanted to say hi.”

“Hi,” he grins, and she returns it readily. For the moment, they’re content with the silence, the enormity of this second—or third, whatever—first meeting. It feels like another beginning. 

Felicity tentatively reaches for his hand, but before he can reach back, they’re interrupted by a loud clanging. They jump away from each other, regaining the space Oliver didn’t notice they’d lost, and look up, probably wearing identical expressions of guilt.

Thea, of course, is climbing the bleacher stairs, smirking up at them with unabashed glee in her eyes. Oliver bites back the groan of dismay if only to keep Felicity from feeling more self-conscious. His sister’s smirk widens, and Felicity jerks to her feet, smoothing her Starling City Prep sweater nervously.

Remaining seated, Oliver tries his best to paste on a nonchalant expression and look less like he’s checking out Felicity’s ass, which is  _right_  there in all its glory. He’s unsuccessful based on Thea’s eye roll.

“Hey, Ms. Smoak,” she calls out, deliberately innocently. Oliver braces for her follow up. “Is Ollie giving you a ride home, too?”

Oliver quickly stands to come to her defense and he knows without looking that Felicity’s face is bright red. “Thea,” he warns, and she guiltily mumbles an apology.

“Thea,” Felicity begins more kindly than his sister deserves, “It’s good to see you again, under better circumstances.”

Thea brightens even as she looks more chastened. “Yeah, thanks again. Roy and I had a lot of fun.” Just when Oliver’s starting to think his sister isn’t an unmannered heathen, she finishes with, “Looked like you and Ollie did, too.”

Impressively, Felicity doesn’t rise to the bait. “I always enjoy getting to speak with the people influential in students’ lives. Parents, siblings, anyone really.” It’s a perfectly diplomatic answer that takes the wind out of Thea’s sails.

Before she can mount a new offense, Oliver cuts her off. “That’s enough, Thea, unless you want to walk home.” So what if all three of them know it’s an empty threat?

Thea’s eyebrows raise skeptically as if she’s about to call him out on it, but Felicity interrupts. She turns to him perfunctorily and extends a hand. Oliver stares at it in confusion and disappointment. This is not how he wants to touch her again for the first time. 

With a conniving grin, Felicity says, “Thank you for your insight, Mr. Queen. Really explains just  _so_  much.”

Oliver can’t help his smirk and he reaches out to gently shake her hand, just barely resisting the urge to pull her closer. “You’re very welcome, Ms. Smoak.” He infuses the words with all the innuendo possible, little sister be damned. Thea’s too busy trying to work out what Felicity meant by her statement anyway.

Still grinning, Felicity wishes them both a good night and bounces down the stairs. He watches her go, ignoring Thea’s repeated questioning of, “What’s that supposed to mean? What did you say about me? Ollie, what did you tell her? _Ollie?_ ”

He shrugs a nonchalant and truthful, “Nothing,” then starts down the stairs himself, Thea and her questions trailing behind.

 

* * *

 

His tendency to let Thea roam as she pleases on weekends pays off because there’s no one home to ask him where he’s going Saturday afternoon. 

Oliver takes one of the less conspicuous sedans, the BMW that says well-off but not filthy rich, and drives to a tract of townhouses outside of downtown. Parking on the street, he notes the red MINI Cooper in the driveway. On the one hand, the compact car is so perfectly Felicity. On the other, it shares a name with the hacker who played a vital role in their separation.

Now he’s just being ridiculous. He rolls his eyes at himself and knocks three times. Not too quickly or eagerly, but just... knocks.

The door opens a few seconds later, and his nerves ease knowing that Felicity was waiting nearby. “Hi,” she greets brightly, a grin blooming on her face. Her eyes linger on him, and he sends a silent thanks to Sara for her prescient text this morning reminding him to wear his brown leather jacket.

“Hey,” he returns with an equally wide grin. She nudges the door open wider and waves him in. “Nice place,” Oliver notes after a cursory glance around, following her into the living room. Being principal of Starling City’s elitist high school must be worth something because she’s clearly doing well for herself.

“Thanks,” she replies, self-consciously straightening already straightened throw pillows. “You want a tour?”

“Of your bedroom?” The question slips out, and Oliver cringes at himself. Felicity doesn’t seem to mind his lack of charm, though, because she’s too busy laughing at him. “I didn’t mean that.”

“Too bad,” she teases. “I can take your jacket, at least.” Her offer is followed by a heated look, and he thinks Felicity’s imagining the same thing he is. Her stripping him of the leather, followed by a tour of her bedroom.

After a loaded moment where they’re just staring at each other, Felicity determinedly turns away. She runs a quick hand through her loose hair and mutters, “God, when did we turn back into horny teenagers?”

Her comment breaks the tension, and Oliver chuckles. “I don’t know. Maybe we just didn’t get it out of our systems the first time around.”

“No, we didn’t get a chance to,” she says with a touch of regret.

That’s not what he wants her focusing on today. Today’s about  _second_ —or fourth, whatever—chances. In a truly uncharacteristic move, Oliver gestures to her dining table and suggests, “Maybe we should talk first?”

“Sure, talking,” Felicity agrees, “We can do that. I’m always doing so much of that.”

“Still?” he teases, and she shoots him a dirty look. “So. Tell me why you became a principal. And you said all my hot-for-teacher fantasies were never going to happen.”

Felicity grumbles at him but she doesn’t look entirely annoyed. “Keep that up, and they won’t.” He grins in the face of her light reprimand. “I didn’t mean to, really. I got my teaching certificate the summer after graduation because I liked tutoring and I wasn’t sure if I’d find a job in computer sciences, misogyny being what it is.”

“And you were a great tutor. Patient, thorough,” Oliver compliments, and she rewards him with a smile. “Really creative with _incentives_.”

“Stop,” Felicity chides, laughing. “I was working freelance for a tech company and also doing some substitute teaching on the side. I ended up liking the teaching more—I felt like I could actually make a difference—so I looked for full-time teaching positions. Found one at a private school that was offering advanced coding classes. After awhile I got sick of the administration telling me what to do, so I started taking classes in education administration. Thought I could get some insider knowledge on how they operate, but once they found out and I finished the degree, they actually promoted me to vice principal. Something about having a female vice principal being progressive.”

“Then how’d you end up in Starling City?” Oliver prompts. It’s no surprise to him that Felicity fast-tracked her way through her career. She’d always been too smart to stay idle and ignore opportunities to educate herself.

“I met Walter at a conference. He liked my ideas for how to move private schools away from coddling their rich students, thought it was very ahead of the curve. He said that his principal was retiring and that I would make a great candidate. I had a couple rounds of interviews, and I’m sure Walter was doing behind-the-scenes campaigning, but yeah. Here I am.”

By her small smile, Oliver can tell Felicity really is pleased with where she’s ended up. And she should be. “But  _Starling City_. It didn’t raise any red flags for you?” he asks, because he’s genuinely curious if she’s thought about him like he’s thought about her.

“It did. Of course, it did,” Felicity sighs and avoids looking at him. “I didn’t just forget about you, about us. I actively had to stop myself from looking you up. I even wrote a code that would delete your name from my internet searches. I felt guilty and I pined and moped, and it was really dramatic there for awhile.”

After a bitter chuckle, she finishes, “In the end, it was too good an opportunity to pass up. And I’m glad I didn’t.” Tentatively, Felicity reaches across her dining table. She doesn’t have to go far, because Oliver’s there to meet her halfway.

“I’m glad you didn’t either. Everything that’s happened? It’s lead us here, to this,” Oliver agrees readily.

There’s no use dwelling on the past. Chances are, they wouldn’t have lasted in college anyway. He was too unstable, not like that but about  _life_  and how to reconcile all his privilege with creating his own path. Not that he knows what that path is, but at least he recognizes that it’s up to him now. And Felicity’s obviously grown miles from the geeky, tutoring, shut-in she was. They barely made sense together as wildly different college students, but they might make actual sense together as adults who know their own minds.

“And where is here? And what’s this?” Felicity questions with a curious lilt.

Oliver’s lips quirk in a hesitant grin. “A second chance, maybe?”

 

* * *

 

“You know,” Felicity murmurs from where she’s resting on his chest. Her fingers idly drum against his bare skin, and he’s surprised by how familiar and comfortable that gesture already feels. “You never told me what you’ve been up to since college.”

Oliver’s glad she’s not in a position to see the grimace on his face. Trying to buy some time, he strokes his fingers down her arm, pleased when she squirms against him. Maybe he could buy himself a  _lot_  more time.

Finally getting to experience the tour of her bedroom was  _interesting_. Oliver can only imagine how much more interesting the full house tour would be. He’ll have to take her up on that another day.

“C’mon,” she cajoles, shrugging away his touch to prop herself up on his chest. She presses a light kiss to his sternum then looks up expectantly, “Reveal your secrets, Mr. Queen.”

“We’re going to explore that later, too,” he says roughly, averting his eyes to her ceiling when she smiles smugly. “How do you feel about assigning me detention, Principal Smoak?”

Her nose wrinkles, and she shakes her head rapidly. “Mmm, nope. Too far. Can’t do it.”

“Damn,” he whines with feigned disappointment. His attempted distraction is only momentary because Felicity hasn’t given up the ghost. She starts poking him in the side, the same way that made him ticklish back then. “Stop it,” he snags her wrists then flips them so he’s hovering over her, “before you start something you can’t finish.”

“Oh, I can finish.” Felicity literally rises to the challenge, leaning up to press her lips to his. Except when he tries to deepen the kiss, she pulls away. “ _After_ you answer my question.”

“Ugh, look, it’s not interesting or impressive or even very long. I’ve pretty much just been dicking around this entire time,” Oliver confesses with an irreverent shrug. Felicity looks disbelieving so he continues, “After I left Boston, I still didn’t really care about anything. My parents were going through one of their rough patches and they didn’t want to create any bad press or scrutiny by cutting me off or punishing me. Keeping up the perfect family image was more important than making sure I grew up into a decent human being.”

Felicity grimaces and reaches up to stroke his jaw comfortingly. “That’s an awful priority to have. I’m sorry, Oliver.”

“It’s not really their fault. I was basically an adult and I had resources and opportunities. I could have made better decisions. Instead, I just threw away several years of my life. The only worthwhile thing I’ve done in years is try to get Thea on track to an actual future.”

She lights up at that. “You’re doing a wonderful job with her. It’s been what? At least three months since your parents “went on vacation,” and she’s not just still alive but her grades are improving and she’s trying out new interests. Her boyfriend’s even an upgrade, and I never thought I’d be saying that about a guy who’s been arrested multiple times.”

As proven by his short chuckle, Oliver shares her incredulity. Then she shifts under him, and he’s brought back to reality. “Can we not talk about my sister and her boyfriend when we’re naked in bed?”

With an embarrassed cringe, Felicity nods enthusiastically. “That seems fair,  _Mr. Queen_.”

“You’re going to kill me,” he groans before pressing her more firmly into the mattress.

 

* * *

 

Oliver fumbles through a pile of their discarded clothes, trying to find his phone before it wakes up a napping Felicity. He’s unsuccessful, though, because she grumbles discontentedly and inquisitively just as he finds it in his jean pocket. He’s also just in time to miss the call.

“Sorry,” he breathes, sliding back into bed. “That was Thea’s ringtone.”

Stirring more awake, Felicity gives him a soft smile. “You should call her back. I don’t know what time it is, but it’s getting a little late, right?”

With a grateful smile, Oliver gives her a quick kiss and draws the blankets back over her. Feeling weird about the idea of talking to Thea while naked, he pulls on his boxers and slips into the hallway so he doesn’t have to talk in hushed tones and give her any reason to be suspicious. Thea just wants to tell him they decided to see a movie so he shouldn’t wait for her for dinner. Oliver fakes his disappointment, reminds her to get home at a reasonable hour, and hangs up with a grin.

When he re-enters Felicity’s bedroom, she’s sitting up in bed, her tablet resting on her knees. His grin grows wider as he announces they have a few more hours. That’s when Felicity hooks a hand around his neck and drags him on top of her while also discarding her tablet then working her hand into his underwear. “What’s this for?” he laughs, because while enthusiasm has never been a problem, this is a whole new level. 

“I think you know exactly how women feel about you when you’re being the doting older brother,” Felicity explains with a sheepish smile.

Oliver shrugs helplessly. “True. But I’m not doing it to impress anyone.”

“No, you do it because you love Thea. And that makes it so much more attractive. It’s really just an unfair self-perpetuating cycle where everything you do makes you exponentially hotter to me.”

“Funny,” he mutters, pleased but confused by her complimenting, “You didn’t seem to have a problem avoiding me after that basketball game.”

Felicity scoffs disbelievingly. “Survival mechanism. You’re stupid distracting. It’s cute you think I could do my job if I thought there was any sort of opening with you. Better to just have you hate me.”

Carefully, he brushes away the shock of hair she’s trying to hide behind. “Even back then, I didn’t hate you. I mean, I did right after, but then it sort of faded away. You weren’t wrong. If anyone has the potential to screw this up, it’s going to be me so I can’t exactly blame you for trying to protect yourself. Eventually, I guess I focused more on the disappointment of us ending and less on the how because it could have easily been all my fault.”

“You don’t give yourself enough credit, Oliver. You were hands down the best relationship—or non-relationship—I’ve had. I always kicked myself for ending it in the worst way possible, for letting my fears hurt you like that.” Felicity quirks a deprecating smile. “I didn’t really want to mention it, but you were a lot quicker to forgive than expected. I kind of figured you’d be mad at me for approximately ever.”

What was he supposed to do? Just ignore his gorgeous, genius ex who happened to be his sister’s principal and who happened to help convince said sister to start investing in her future while sticking her neck out for her happiness? Talk about next to impossible.

Young and dumb Ollie might have tried to get her fired, but older and wiser Oliver could see that all of Felicity’s accomplishments since the last time they saw each other was just more proof of his outpunting his coverage when it came to her. 

“Well, if you still want to make it up to me...” he raises a suggestive eyebrow.

To his surprise, Felicity's fully on board, pushing on his shoulders till he's flat on his back and she's hovering over him. “The last time I sat in your lap like this, we were _both_ naked.”

Oliver’s eyes slam shut at the reminder of their last time in college, when he’d given Felicity free rein to experiment and figure out what she liked. He had the  _best_  time as her assistant. So much so, a repeat sounds like an excellent idea.

“Is that a suggestion?”

“ _Absolutely._ ”

He's never gotten out of his underwear faster.

 

* * *

 

“I don't think grocery runs are supposed to take this long," Felicity points out logically even as he grumbles about getting redressed, “Besides don’t you guys have a cook who orders groceries from a supplier?”

“No?” Oliver tries before giving up the half-lie. “Okay usually, but since it’s just me and Thea right now, I do the grocery runs. Trust me, Thea will find a grocery run way more believable than me being out at a club or something. Tommy’s so disappointed with my lack of wingman’ing, he probably wouldn’t even lie for me at this point.”

“Wow, this is really starting to feel sordid,” she rolls her eyes. “I never snuck around in high school. Is this how it usually goes?”

Thankfully, Felicity sounds more amused than hurt that their second chance has so far been confined to the occasional and brief evening or weekend interlude whenever he can sneak away from the house and Thea.

As a thank you for her understanding, and because he has less and less self-control around her, he leans down for a lengthy kiss that almost has her dragging back into bed. “I’m sorry,” he apologizes breathlessly for the umpteenth time, “We’ll figure it out—”

“After graduation,” Felicity finishes for him with a knowing look. Right. Aside from Thea’s feelings and perception at the school, it’s more Felicity’s reputation on the line than anything else. 

He flashes an agreeable grin then goes back to shrugging his shirt on. When his head emerges, Felicity’s looking down, picking at a loose thread on her comforter. “You know, just while we're on the topic, I mean, back then, we never DTR’ed as the kids may or may not still say. I really have no idea. But that apparently lead to a lot of complications and miscommunication. So this— _us_ —we’re a thing... again... right?”

“I don’t really know what DTR means, but if by “we’re a thing,” you mean you’re my girlfriend and I’m your boyfriend. Then, yeah, we’re a thing,” Oliver confirms with a teasing grin. Felicity kicks a foot out to push against his knee in annoyance but leans up to accept yet another kiss.

"Bye, boyfriend," she smiles gleefully, and he returns the sentiment with an equally wide smile.

 

* * *

 

“Where have you been, and why is there a goofy-ass smile on your face?”

His head is currently buried in the fridge while he puts away the milk so Oliver has no idea how Thea knows that he’s smiling but she’s not wrong. Straightening up, Oliver attempts to school his expression into nonchalance even as he invites Thea to take a seat at the counter. His sister watches him suspiciously while he scoops them both bowls of ice cream before joining her.

“Remember when I was trying to convince you that I wasn’t trying to ruin your life by making you go to school? And I told you about my tutor who I dated for awhile?”

“Yeah, of course. You admitted to having actual feelings. For a girl. It’s kind of rare.” Thea suddenly whirls towards him and groans, “Oh, Ollie, tell me you didn’t go full stalker and track her down.”

“What? No!” he immediately denies. “Why do you always assume the worst about me?”

“Because it’s usually pretty close to the truth?” Thea offers with a little shrug.

After a silent prayer, Oliver looks back at her. “I’m trying to tell you something important here.”

“Oh. Okay.” Thea gives him her full attention this time, and it kind of makes him want to squirm. “What’s up? Have Mom and Dad just completely abandoned us? Because it’s starting to feel that way.”

“I’m sure they’ll be back,” Oliver mutters evasively because she’s still not wrong, “for your graduation. I hope. That’s not what I’m trying to tell you.”

Her spoon clatters into her mostly empty bowl. Yeah, there’s the other reason he calls her Speedy. “What are you trying to tell me? Because this just feels like stalling.”

“You’re the one who brought up Mom and Dad,” he counters before realizing he’s falling into it again. “Look, I’m trying to tell you that the girl from college, the one I tried to straighten out for—”

“Your one and only,” Thea interjects on an exaggerated sigh.

“Uh, no. I mean, I don’t know. But she’s—”

“—your long lost love.”

“Thea.”

“—your soulmate.”

“ _Thea._ ”

“—your one true love.”

“This is getting repetitive.”

That gets her attention. Thea cocks her head and asks, “But not annoying?”

“No, it’s been annoying but now it’s repetitive,” Oliver clarifies.

With a grin, she continues, “Your one and only, long lost, loving soulma—”

“Felicity!” It’s Oliver’s turn to interrupt her. “Felicity. She’s Felicity.”

Thea pauses as if she’s running through her mental contact list then shakes her head. “ _Who?_ ”

Of course she knows who Felicity is. Oliver’s confused before he remembers how he was as a teenager. Teachers didn’t exist outside the school. They didn’t have lives, they didn’t have families, and they definitely didn’t have first names.

“Uh,” he stutters because this is definitely more difficult now that it’s not an outburst borne of frustration and annoyance. “Felicity. Smoak. That girl was— _is_ —Felicity  _Smoak_.”

“My  _principal?!_ ” For all her obvious hinting, Thea’s incredulous, maybe even disgusted. “Your college ex-girlfriend, who broke your heart and dumped you and basically turned you into an emotionally constipated dud, is my principal?”

“She did not do any of those things,” Oliver denies before reconsidering, “Okay, she kind of did the second thing.”

“Dumped you,” Thea repeats bluntly, “You can’t even say it out loud. And you’ve known this entire time? You didn’t have some kind of, I don’t know, facial amnesia where you blocked out what she looked like for all these years but you were hit on the head last night and now you can remember?”

He furrows his eyebrows in confusion. “That’s... an oddly specific scenario.”

“I’m just trying to come up with some reasonable explanation for why you pretended for months not to know who she is and then  _lied_  to me about there being nothing going on with you two.” 

Her voice has gone high-pitched and sharp, and Oliver winces. He may have gone about this in the wrong order. Trying to solidify things with Felicity before telling Thea about them. But doing it in the reverse—telling Thea of his intentions before things with Felicity progressed—would have made him uncomfortably vulnerable in a way that was never going to happen.

So he resorts to what he does best: half-truths. “I didn’t lie to you. There was nothing going on between us.”

Like someone who's known him her entire life, Thea doesn't buy it, and her scoff is offended before she spits out, “ _Was?_ ”

“See? When you’re paying attention, you’re actually really detail-oriented and—”

“Don’t," her look is almost murderous, "Do not try to turn this into a thing about how I should be an editor or something. Not what’s important right now. Forget semantics. You  _lied_  to me.”

“Thea,” Oliver interrupts loudly. When he has her attention, he sighs, “I wasn’t trying to lie to you. I was trying to lie to myself. I didn’t want to remember her. I didn’t want to remember having feelings for her. I just wanted to move on. Finally.”

The confession works because Thea’s stance softens entirely. “But you couldn’t?“ she prompts with all the hopefulness of a teenaged girl who just realized she’s been witnessing a romance novel come to life.

“No, I couldn’t. And Felicity couldn’t either. So we’re... dating.”

“How long?” she asks curiously. “Actually, never mind. You’ve been oddly smiley and randomly disappearing for, like, weeks now. Guess that answers that.” 

Thea doesn’t squeal or anything so cliche but she does bite down on her lip to suppress a smile. Then she throws her arms around his neck, almost toppling them both off the stools. “Great, good, I’m really happy for you.“ Finally, she pulls back, eyes wide and disbelieving. “Am I going to have to call her Felicity now? Because, weird.”

Oliver grins a little because Mr. Steele had made the request for him to call him by “Walter” and Oliver cringed so hard his face hurt after. “We’ll worry about that after you graduate.”

“Wow, like an actual month from now?” Her tone is mostly teasing, but neither of them can deny the truth of it. “You’re thinking that far— Do I hear wedding bells?”

“Hilarious,” he grumbles, tousling her hair in a way that starts an all-out war.

 

**Notes for the Chapter:**

> I apparently underestimated the legs on this thing so will need another chapter to wrap things up.


	4. Chapter 4

When he shows up one day at Felicity’s place, he’s inexplicably nervous. Probably because he’s holding a note from Thea to Felicity that she demanded he not read before shoving it into his hand. Oliver doesn’t think it’s anything bad. He knows Thea likes and respects Felicity—Principal Smoak, he means—and he knows she knows how much  _he_  likes Felicity.

Still, he gives her the folded paper with a wary look on his face that she reciprocates right back. “What’s this?”

“Not sure,” Oliver admits with a hopefully casual shrug. “It’s from Thea, but she asked me not to read it.”

“And you didn’t?” Her eyebrows raise in a teasing yet impressed way, “What a trusting older brother.”

Yeah, he kind of is, but also, “She’s come a long way. Earned some of that.”

Felicity makes a sound of agreement as she unfolds the paper. Her eyes skim back and forth across the page, line by line once then twice. Then, to his absolute horror, Felicity bursts out laughing.

All of a sudden, Oliver’s mind is flooded by the embarrassing things Thea could have told Felicity. He should have thought of that in the first place instead of talking himself down from thinking it was a death threat or something equally ludicrous. He makes a grab for the paper, but she hides it behind her back and slips out of reach around her kitchen island.

“Let me see it!”

The demand sends her into another fit of laughter that sets off his laughter as well. Pretty soon he’s wrapped around her in a sorry excuse to try to steal Thea’s note. The paper flutters to the kitchen floor as he picks her up and carries her to the couch. It’ll be a few hours before he remembers to retrieve it while getting them water.

_Dear Ms. Smoak,_

_Please excuse Oliver Queen’s lacking skills as a boyfriend. I assume he hasn’t done his homework and brought your favorite flowers or anything equally romantic. He’s obviously out of practice so feel free to keep him at study hall through dinner and breakfast. We will never speak of this again._

_Sincerely,  
Thea Queen_

Oliver’s in the middle of swearing up and down to make himself an only child again when Felicity interrupts by sliding her arms around his waist from behind. “It’s sweet,” she murmurs against his back, “Thea’s trying to tell you that she approves.”

“She’s trying to make sure I die of embarrassment and make you think I’m a shitty boyfriend,” he corrects with an annoyed sigh. Yeah, he knows what she was going for. Like a note so a kid has permission to go to doctor’s appointment but a note so he has permission for an overnight date without feeling like he has to rush home for Thea. It’s still mortifying.

Whatever. He can think of better things to focus on when Felicity’s naked. Oliver plans on taking full advantage of this “hall pass” and dealing with his shithead sister tomorrow.

 

* * *

 

When he pulls up to the manor the next afternoon, there’s a limo in the driveway, and an actual pile of suitcases spilling out of the trunk. He texted earlier to let Thea know he was on the way so she could clean up her ulterior motive for getting him to spend the night at Felicity’s. Well, that would explain why he didn’t get a response.

 _Oh shit_.

Leaving his car running, Oliver sprints inside and follows the yelling to the hallway outside his and Thea’s bedroom.

“Welcome home!” he interjects loudly, ignoring his father’s red face, his mother’s literal pearl-clutching, and Thea’s state of not entirely dressed. Oliver can only imagine where the hell Roy is.

Everyone stops in their figurative tracks and turns to stare at him with wide, disbelieving eyes. Thea takes him in, and then as if suddenly remembering where he’s been, grins, and rolls her eyes  _hard_. Their parents look just as unimpressed at his sudden appearance.

“Oliver!” Robert’s voice is  _loud_ and  _strident_ , “When we left you in charge, we were under the distinct impression that you would actually step up and take care of your sister. Instead we come home to find you gone to some place Thea won’t tell us, and her in bed with a boy from the  _Glades_.”

Oliver jerks back. While he knows the situation looks bad, it’s really not. He was just at his actual girlfriend’s house—kudos to Thea for holding strong on that one—Thea’s grades are up, and Roy is a major improvement over  _Dalton_ , who he knows his parents have caught sneaking out of the house.

“Look, it’s just a—”

“Do not say misunderstanding,” Moira interjects with an arched eyebrow. 

“But it is,” Thea counters just as archly. “This is literally the first night Ollie has spent away from the house. He drives me to school every morning, he picks me up every afternoon, my grades are better, and my boyfriend isn’t some douchebag with a trust fund who thinks he can treat me like crap. What more do you expect after you guys just pack up and leave for, like, half a year and barely remember to check on your own fucking children?”

“Language!”

The admonishment comes from all three of them, but Thea looks unrepentant. Her expression settles into a surly pout before she continues, “You don’t get to peace out of our lives for the better part of a year and then come back and judge how we handled it. Which is honestly going a lot better than everyone expected.”

Oliver nods emphatically, “What she said.”

Their parents exchange a look before capitulating for the moment. “We’re going to oversee unpacking and then we’ll discuss this all at dinner. Thea, your...  _guest_  is not invited,” Moira advises pointedly.

“That’s rude!” she calls to their backs, “And I don’t want him to meet you guys like this anyway.”

Oliver smothers a grin and shares his own look with her.

“Fuck?” Thea asks tiredly.

“ _Fuck_ ,” he agrees just as tiredly.

 

* * *

 

 “Sorry I’m such a disappointment but I did the best I could,” he grumbles, pushing around the food on his plate. He cops a look for his immature behavior, but whatever. “Thea’s right, okay? You guys just left us here so if you don’t like how I handled it, then maybe next time don’t abandon your teenage daughter with her dipshit older brother.”

They exchange another tired look, and if they got any rest and relaxation during their holiday, it’s no longer apparent. This has been going in circles for nearly an hour, and Thea gave up awhile ago, storming off. He hopes she’s in her room since she has an early start on Monday mornings.

“Look, why don’t you get some rest? I’ll take Thea to school in the morning, and we can talk about it later.”

“I don’t think that’s a good idea, Oliver,” Robert starts, “I mean, you taking Thea to school. She needs to get back to her regular routine.”

“Her regular routine involved getting dropped off by one of the drivers and then sneaking off campus to wherever. At least when I drop her off, she stays there,” Oliver points out logically. When they look at each other in surprise, he sighs, “Did you really have no idea or did you just not care?”

He leaves that question lingering in the air and pushes out of his chair. Scuffing his feet the entire way down the halls, he pauses outside Thea’s room, hearing the telltale sounds of angry drawer slamming.

“I’m still taking you to school tomorrow,” he announces to the door during a pause in the racket.

A beat passes. Then another. “Okay.”

 

* * *

 

The next morning, he comes back from the school to find his mom in the kitchen, sitting on the same barstool where he told Thea about Felicity. She’s dressed in a robe and sipping on her coffee while browsing the paper, and the sight is so missed he almost smiles.

“Morning,” he manages in a more polite tone than the ones they used last night.

Moira startles a little and sets down her mug before waving him over to join her.

“Dad go to the office?” he asks, already knowing the answer.

She nods quickly in affirmation then bluntly asks, ”Oliver, will you at least explain to me where all this talk of you being a disappointment is coming from?”

“Don’t act like you’re not, Mom. It’s not like I’m Carter Bowen,” he points out easily.

“The Bowens are insufferably smug,” Moira sighs, “You know that as well as I do. Don’t avoid the topic.”

Oliver huffs a chuckle because she usually avoids saying things like that outright. At least she puts up a good enough front at pretending to like them at social events, but that’s always been one of her strengths. “I just woke up one day. I mean, kind of literally. Raisa said something about Thea ditching school again, and I realized I’ve never set a good example for her.”

“The one time I tried back in college, I just gave up the second I hit a roadblock,” he knows better than to tell his parents about that drama especially with Felicity still Thea’s principal for another month and them secretly dating, “After I came home, you and Dad were having problems, and my screw up didn’t rate.”

“That’s not”— Moira sighs at the look he gives her—”You and Thea are right. As much as we love the two of you, we have not paid as much attention as we should have. Spending money isn’t the same as spending time.”

Oliver’s taken aback by her easy agreement. Maybe this trip did do more good than he expected. “It might be too late for me, but Thea. She’s doing a lot better in school. Her grades are pretty decent now, and she joined some clubs. She wants to go into fashion design.”

Moira’s expression tells him she disapproves of the choice, but her words are more measured. “That’s remarkable, Oliver. I love you even more for encouraging your sister’s passions. But you’re wrong about one thing. It’s not too late for you.”

Shaking his head, he reminds her, “Dad won’t even give me a job at QC.”

“Do you want a job at QC?” Moira counters immediately with a knowing look. Resigned, he shakes his head again, this time in denial. “Exactly. Once you figure out what it is you  _want_  to do in life, I’ve no doubt you’ll excel at it, Oliver. And you will one hundred percent have our support.”

“Thanks, Mom,” he murmurs, ducking his head in embarrassment before leaning over to kiss her cheek. “For now, I think I’m good with playing Thea’s chauffeur until graduation.”

“You know,” she muses, “Somehow, I think that’s what Thea wants as well. I didn’t say it before, but it’s so lovely to see how close you two have become.” 

Oliver grins wide at his mom because he’s really enjoyed it, too, but then she reaches over to pat his leg and continues, “Now, tell me how she met this Roy character. Thea seems quite attached already.”

The blood just about drains from his face.

 

* * *

 

The conversation with his Dad never really happens. He figures Moira relayed the specifics, but Robert stays just a little skeptical of his sudden aboutface. Still, it’s not too long before they’re all seated at the Starling City racetrack to observe Thea’s (earned) high school graduation.

Starling City Prep doesn’t limit the number of allowed guests so Thea’s got more of a cheering section than their small family warrants. In addition to the three of them are Raisa and some of the other long-standing staff members, Tommy, the Lance sisters, and poor Roy, who’s determined to make a good impression in his suit despite the uncommonly warm day. Thankfully, by now, he and Tommy have adopted the kid as a younger brother of sorts and provide a decent buffer against his still prickly parents.

Felicity’s wrapping up her remarks, which he’s heard too many times before today, when Moira leans over to whisper in his ear, “The new principal is younger than I expected.”

“The students like her,” Oliver whispers back, just in time for the graduating class to break out in thunderous applause, despite the mulish look on some of the board’s faces. “She’s very smart and well-respected.”

“Hmm,” Moira hums contemplatively, “I would have liked to meet her, but those parent-teacher conferences are so tedious.”

“I  _know_ ,” he rolls his eyes, “I went to all of them while you guys were gone.”

Robert leans forward suddenly to stare at him until Moira pushes on his shoulder to ease him back into his seat. Oliver rolls his eyes again to himself.  _Yeah, that’s right, Dad, stepped up even more than you gave me credit for._

They sit through the valedictorian speech and more than half the alphabet before Thea’s row stands to line up at the base of the stage. When her name’s called, Oliver’s on his feet, whooping and hollering with the rest of the crew. For once, it causes his mother to smile instead of shush them.

Thea accepts the rolled up piece of paper, which is mainly for show, before hugging Felicity. He can practically feel his mother’s antennae rising but refuses to look at her. She gets to the other side of the stage before moving her tassel over and smiling into the cameras set up there.

“Thea seems to know Ms. Smoak well,” Moira comments once he’s taken his seat again. Oliver mumbles noncomittally, but that, as usual, doesn’t stop her. “See? That’s the type of women you should associate with, not whomever you’ve been hiding since we’ve come home.” 

Her comment isn’t as quiet as she thinks, or maybe she just did it on purpose, because Tommy on his other side chokes on his complimentary sparkling water.

 

* * *

 

They have a small celebratory dinner at the manor before Thea and Roy depart for some lavish senior night the school arranged. 

To counter the binge drinking parties common of previous years, Felicity tasked the class president with organizing a non-alcoholic party that would still entice the students into attending. Somehow, they landed on an all-night cruise aboard a ship outfitted with basically the entirety of a family fun center. Through sheer persistance and adherence to their parents’ newfangled rules, Thea and Roy have earned some leeway so no one bats an eye when they head out.

That means he’s free to show up at Felicity’s house with celebratory champagne, letting himself in with his key. No, _Tommy_ , it’s not too soon for him to have a key, unlike that certain phrase that’s been on the tip of both their tongues more than once recently. She’s curled up on her couch, fuzzy socks and sloppy bun, so he knows she isn’t expecting him.

“Hey,” she grins, leaning up when he leans down for a kiss, “I thought you’d be with the fam tonight.”

“No, Thea and Roy are on that cruise so there’s no point at staying home.” He pops the cork, ignoring her mild rebuke to watch where he’s aiming that thing, and offers her the bottle, not bothering with glasses. “Congratulations on graduating your first class, Principal Smoak. My mom noticed that hug by the way.”

“I wasn’t going to  _not_ hug her just because your parents were there,” Felicity rolls her eyes even as she takes a hearty swig of champagne.

Oliver doesn’t bother to hide how her expert handling of the bottle is an amusing turn on. ”Yeah, well, now you’re on my mom’s radar. She thinks you’re the type of women I should be “associating” with instead of my usual crowd. Tommy choked on his water when he heard her say that.”

“Your usual crowd? LIke maybe Mrs. Fuller?” He stiffens up and not in the good way. “Yeah, totally noticed that little exchange when you were taking photos. Is that why you and the Fuller boys don’t get along?”

“In my defense,” he begins slowly, not entirely sure how she’s going to react, “they were divorced at the time.”

“You are such a cad,” she scoffs, dismissing his very reasonable excuse. “I can’t believe I have to publicly admit to dating you now.”

Oliver brightens at her response, the way she doesn’t hold his past against him and the way she’s talking about their future. “Yeah? When do you think that’s going to happen?”

“You’re more familiar with the dog-and-pony show than I am. Do we, like, release a statement? Have Thea post an adorable selfie with an expertly crafted caption? Ambush your parents at a press conference? None of these, by the way, are serious suggestions. Please,  _please_ , do not follow through.”

Her voice turns desperate by the end, and he laughs a little because, yeah, they’re all in the realm of standard operating procedure. “Maybe just dinner?” he suggests, shifting her over on the couch so he can fit on it, “We’ll figure out something that’s more  _us_.”

“Mmm, I like the sound of that,” Felicity agrees, handing him the bottle so she can better cuddle into his side. “Hey, I haven’t wanted to push, and we’ve both been busy, but how’d your talk with Captain Lance go?”

Oliver nods, feeling his heartrate accelerate at just the memory. The captain still makes him nervous, even though he does his damnedest not to show it, and this project is the first time in a very long time that he’s put himself out there. Laurel and Sara did their best to try to butter up their dad, but honestly the captain just likes to watch him squirm.

“I did. He’s on board, reluctantly, I might add. I just have to figure out the logistics,” he offers, trying to downplay it. Felicity doesn’t let him. She springs up, only to hug-tackle him at a different angle, one that fully splays her out against him. He’s not complaining. “Hey, I haven’t done anything yet.”

“You will,” she states assuredly. “You already have your next steps. Form the 501(c)(3), which Laurel is going to help you with, and hire Roy. That’s more than enough to get the ball rolling.”

Nodding, Oliver basks in her enthusiasm and praise. The idea came to him while watching Felicity clean out her closet, of all things. The afternoon he spent with Roy in the mall trying to find a suit for prom was the first of many. His sister’s boyfriend often asked him to accompany him on shopping trips as his disposable income increased and he wanted a less thread-barren wardrobe. 

Oliver quickly realized that most young people in the Glades didn’t have the means to look presentable and make a good first impression. Sure, there were thrift stores, but they were often poorly organized and lacking in quality garments. The closets of Starling City’s elites and even upper middle class like Felicity, on the other hand, were full-to-bursting and in need of more than a little spring cleaning.

With that in mind, Oliver decided to start up an organization that would encourage the better off to liberate their unworn clothing so that kids, young adults really, from the Glades would have a chance to “go shopping.” The idea was to get them at least one outfit that would work for a job or college interview or something so they could better fake it ‘til they made it. He and Thea were raised on the importance of appearances, and he’s seen the transformation in Roy’s confidence as his wardrobe slowly upgrades.

Of course, he and Thea, on a gap year despite the fact that they’re not at all European, would be the face of the organization to the elites, while Roy would legitimize it to his crowd. He was soliciting Captain Lance’s support as part of his second chance programs for at-risk youth and also to introduce the concept of poor kids from the Glades suddenly running around in (secondhand and legally obtained) designer clothing. The captain rolled his eyes at the last part, but they both know it’s going to be a hard adjustment for the uniformed officers.

There are similar organizations in other cities that Oliver wants to contact for ideas and best practices. He still needs to get his mother to pitch all her philanthropic groups on donating. Felicity’s already promised to give a hard sell during summer school and once the new semester starts.

It’s a lot to do, but for once he’s excited about the next few months. Finally, he’s setting a good example for his sister. On top of that, he gets to be with his amazing girlfriend in public and, just maybe, do something good with his life.

 

**Author's Note:**

> Slightly better quality images at the [Tumblr](https://smewhereelse.tumblr.com/post/177529711912/)
> 
> .


End file.
